1st and North: How likely is it the Chicago Bears draft Caleb Williams... and keep Justin Fields?

CHICAGO, Ill. - The Chicago Bears have to make a decision on their quarterback position this offseason.

Do they keep Justin Fields and build around him, or select Caleb Williams and try and build a roster with a talented quarterback on a rookie contract.

But, there is a third option.

How likely is it the Bears decide to just do both? Can they keep Fields and draft Williams this offseason?

It is possible. It has worked in the past, too. 

Why the Bears could keep Justin Fields and draft Caleb Williams

Think back to 2004. There was a moment of panic in the San Diego Chargers draft room. Eli Manning did not want to play for the Chargers.

What did the Chargers do? They traded Manning for Philip Rivers, even when they already had Drew Brees.

Brees had been the starter in San Diego since 2002. He, eventually, would piece together a historic NFL career. No one knew that in the spring of 2004.

With Rivers and Brees, the Chargers decided to give Brees a shot at keeping his starting job. Brees would win NFL Comeback Player of the Year in 2004 and win 12 games.

After drafting Rivers, Brees would play in San Diego for two more years before eventually departing for New Orleans in 2006 on a six-year, $60 million contract. Rivers stepped in and began his eight-time Pro Bowl career.

Brees would go on to win a Super Bowl with New Orleans; Rivers would come short of making a Super Bowl in 2007, which was his only AFC Championship Game appearance. The bottom line is both benefited from being on the same roster.

"I like to think that for those two years, we brought out the best in each other," Brees told the Associated Press in 2018. "It was a great learning experience for both of us. I think we both got a lot better as a result of it."

This is one example that's a fairly applicable comparison, since Brees played well in his first two seasons as a starter but wasn't consistent enough to win games.

Sounds a lot like Fields, no?

Giving Fields one last shot at the Bears starting quarterback job makes sense for a couple of reasons. 

First, the Bears have a new offensive coordinator who has experience resurrecting quarterback careers. Why not give Shane Waldron a shot at working with Fields?

Second, the league seems obsessed with using Mahomes as a comparison to Williams. Mahomes, in 2017, sat behind Alex Smith for a fill season before taking over in 2018. Would it be a bad idea to give Williams to adjust to the NFL before having him take the reins?

There isn't much of a sample size with this kind of option, mainly because it rarely happens where a starting-caliber quarterback and a top-five draft pick are kept on the same roster.

Usually, the top-five draft pick is asked to start right away.

Why keeping Fields and drafting Williams doesn't make much sense

Giving Fields a chance to prove he can be a starter in Chicago and giving Williams the chance to get acclimated to the NFL is a great option on paper.

It makes all the sense in the world and is a deviation from what the Bears have done with first-round picks at quarterback in the past.

However, there's one development that could make that difficult to commit to.

ESPN's Adam Schefter has reported recently the Bears could fetch a second-round or even a first-round pick in the 2024 NFL Draft in return for Fields. 

If that's the case, it's hard to argue the Bears should hold on to Fields. 

The biggest argument to keep Fields and trade the No. 1 overall pick is due to the haul the Bears would receive in return. NFL Network reported the Bears would demand a historic haul for the pick, which would most likely include three first round picks and more that could line the Bears roster with top-talents.

If the Bears can get a first-round pick in return for Fields, that would be too good to pass up. 

It would give the Bears a chance to trade back, acquire more draft capital in the first three rounds or even select another player in the first round if the right player falls.

It's just an option.